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John McMahon
Welcome to the Revenue Builders Podcast, a.
John Kaplan
Weekly show featuring B2B sales leaders and executives. Hosted by five time CRO John McMahon and Force Management Co founder John Kaplan, the show goes behind the scenes with.
John McMahon
The people who have been there, done.
Podcast Narrator
That, and seen the results.
John Kaplan
If you enjoy our content, please subscribe, rate and review the show to help us reach more people.
John McMahon
Revenue Builders is brought to you by Force Management.
John Kaplan
We help companies improve sales performance, executing the growth strategy at the point of sale. Find us@force management.com Enjoy today's episode.
Podcast Narrator
Hello and welcome to the Revenue Builders podcast. I'm John McMahon and in this episode I've curated some special moments, some gems, some fantastic insights from a few Chief Revenue Officers. You'll hear what it's like to be the first salesperson into a raw startup, why it's vitally important for leaders to give their people a purpose, how to keep your top sales performance from leaving your company, why execution of all the details in a process matter, and other wisdom shared. On this podcast, we'll hear from Mark Roberge, former CRO@HubSpot, current Harvard sales professor and managing director of Stage 2 Capital, Cedric Pesh, the current CRO@ MongoDB and current CRO at Snowflake, Chris Degnan. There's Certainly many other CROs that provided valuable insights on the podcast, and we'll need to cut in another episode with their gems at a later date. Let's start with Mark Robash. One of the most talented people I've ever met. Mark was the first CRO at HubSpot, and today Mark is a Professor in the Entrepreneurial Management unit at the Harvard Business School, teaching entrepreneurial sales and marketing to MBA students. And he's also co founder and Managing Director at the VC firm Stage 2 Capital. Now, for those of you that want to start as a CRO in a raw startup with no revenue, no leads, no sales reps, Mark describes some of his key challenges when he started at HubSpot as a CRO and the first salesperson.
Mark Roberge
Yeah, so the CRO title is kind of a joke when you have four employees. You know what I mean? You have to kind of, you know, titles don't tell me much when I'm talking to other folks and it's like, hey, back it up for a second. How many employees do we have? How many salespeople do you have? Do you even have frontline managers? If you have frontline managers, do you have a, do you have a sales director layer that manages the managers? And I think that kind of tone sets the Stage for like, what that looks like. Because, you know, when I went in there, we literally had four employees. It was Halligan, Dharmesh and Mike Volpe. Volpe kind of doing marketing, Dharmesh like, you know, doing some coding, and Brian kind of running the show. And, you know, so of course I was salesperson. You know what I mean? Yeah, my title was VP of sales, but I was salesperson. And I. Brian and I closed the first hundred accounts. And, you know, that's, I would say, at that stage. And I've kind of written a lot about that and taught a lot, a lot about that. That first sales hire is so different than your tenth one, right? It's like the tenth one. Like, you show up and you're like, okay, where's the playbook? What's the comp plan? Where's my named accounts? What's the icp? Let me go make some money. That doesn't exist on salesperson number one. Right. Like, you're almost like product manager plus salesperson. Like, this is usually when they bring that first salesperson in. It's like, this is the first moment that the company is going to go from like, maybe five customer conversations a week to like 30. And so that's such a big opportunity for learning. And you're trying to bring in those first deals in a really scrappy way. I personally don't think, like, pricing matters a lot right there. I think you're just trying to get people in and create success stories and you're trying to get good market learnings back to the product team. And so, yeah, I got up to like 100 customers. And then Brian's like, okay, great. Like, this thing works. We feel like we have product market fit. Your new task is hire one salesperson a month. So now you're like, now you're like sales manager, right? And so. And I kind of looked at that moment and I kind of like, that's kind of step two, right? Step one is just the selling. And like, I actually set up the CRM dashboards even when I was the only seller, John. Because I knew if I succeed, I want to set that tone for the. For the culture. And I had such a unique situation where most sales leaders come in and try to, like, instrument things and the old culture and the old guard is a little resistant. I was the only old guard, and I was just doing this. So when the new salespeople came in, they were like, oh, yeah, this is just how it works. I mean, Robert did it from the beginning. And so now all of A sudden you're sales manager and it's all about like hiring people, onboarding people, coaching people and getting them to their number. And then there's an aspect of demand gen as well. And so as I looked at that, I'm like, oh my gosh, I gotta hire one rep a month. And I had like, I had a picture of like what an A plus job would be for hiring, what an A plus job would be for onboarding and what an A plus job would be for managing. And I was like, that all adds up to like 150 hour work week. I can't do it. So I'm like, where am I going to do an A? I can work 80 hours, okay? So like where am I going to do an A plus job and where am I going to try to get by on a B minus? And when I thought about, I'm like, I have to do an A plus job on hiring and I'll do a B minus on the other two because like if I, you know, if I do a B minus job on hiring and an A plus job on onboarding and managing, I'm still dealing with B players. But if I do an A plus job on hiring and get A players in, even though the systems aren't perfect in the process, A plus players are going to find a way to win. So that's like a really important moment for me of like. And I think for folks who maybe get up to that layer, it's like, you know, I spent maybe like a third to half my time on recruiting and interviewing.
Podcast Narrator
Mark had a very interesting methodology to get salespeople that wanted to be managers self select in or self select out of the management role.
Mark Roberge
Let's see, I think I promoted over 20 managers during my tenure. So I had a decent amount of like pattern recognition and experience and what that looked like. All but one came from inside. Good and bad. Good and bad, right. I think it's like it was good in the sense that like I had a pretty good success rate I think with my managers. You know, if we just look at like manager quota attainment, it was very high. I would say it was like 90 plus percent. So I didn't have a lot any folks who were like struggling to build that team, et cetera. And it's because I built this regimented process. I think the mistake there that people make is they promote their best rep to manager. They just feel pressure. And you both know that's kindergarten level. But a lot of people don't know that. And there's A lot of rigorous research to show that's bad. And it's like, well, how do you have a team of 10 people and this one person's killing it and they're number one and they want to be manager and how do you tell them no and promote the number three person, right? And it's like, well, because the job of salesperson and manager is so different. Like salesperson's going out, you know, doing great discovery, moving people through a process, being good with your time. Sales management's all about like picking people and empathy and understanding, connecting and coaching and discipline. Like it's a very different job. And, and so I put together a process of like, oh, you want to be a manager and you want to be manager and you want to be a manager. Okay, here's the process. Step number one, hit your quota six months in a row, right? Cause like I'm not promoting my best rep to manager. But I also, if you don't hit your quota, you're not going to have any credibility. All you have to be, I don't care if you're 180% or 100%, you have to be above 100% to be qualified. Okay? So hey, you're quota for six months, you do that, you're going into leadership school. I architected like a 12 week course with 12 different readings on like managing conflict, building team spirit affected, giving negative feedback effectively. Like basic stuff that I grabbed out of like Harvard Business Review for five bucks. An ebook, you know what I mean? I just had them read it and I did role plays with them. It didn't take much time and I was spending time with my best people. So you go through the 12 weeks, then the next, the final step is you hire a replacement, you keep your quota, you keep your individual quota, you hire one rep and you coach them for three months. Okay, I'm not trying. I hate the team lead thing. I think you guys do too. I hate the like, oh, you have three reps and a quota for like two years. No, I hate that too much. It's too. They choose yourself and not your team, right? But this is just a temporary three month thing. You carry your quota and you manage just one rap. And by the way, like when you have an eight person team, how much time do you have to spend with one rep anyway? A week, four hours. That's all I'm asking you to do, right? So, so then by the time they go through that, it's like first off, two thirds of them drop out of the process at some Point. Right. They self select. I didn't know this was the job. And then by the time they get into it it's like okay, I've worked with this person for multiple years. I put them this through this long process. I saw them actually do the job for three months. So that worked really well. The downside is I never hired anyone from the outside.
Podcast Narrator
Here Mark discusses why there's no great universal sales rep hire across every company. He describes how your hiring profile needs to align with the context of your go to market issues like your use case, the Personas you call on, cold calling branding and other issues which forces you to build a customized hiring profile.
Mark Roberge
Yeah, I think it was my eighth hire in that first year there was a salesperson I'd been courting for a little bit and they were the number one salesperson from a company that probably had 800 salespeople, probably 5,000 employees and they were public. Right. So you can picture this company and I thought it was pretty impressive. Like number one for multiple years out of an 800 person team. That's like pretty good. That's really good. Right. And they were actually kind of bored and wanted to find the next big thing and they decided, decided to come over and I was just, I was like got a little nervous to be honest with you of like you know, managing this person and, and but also excited to see what that type of like performance looked like. And I was shocked that six months later they weren't number one on our small eight person team. And I really, that's when I realized that there is no universal top sales hire profile. But it's very contextual to your go to market context because they were coming from a company that was 15 years old, a value prop that was extremely well understood. Within 30 seconds you knew that what they were selling just by mentioning the company because the company was running super bowl ads. So you can imagine the type of person that succeeds there compared to what we had which was 20 people in a garage across from MIT hawking like HubSpot which no one knew what it was hawking inbound marketing software, which no one knew what inbound marketing was. I mean it's just a completely different sell. And so I kind of break down context for my students is what are you selling to who and what are the context of your company like stage and culture and that kind of stuff. And are you in Japan or are you in North America? Because that matters. Right. So it's those three pillars that define context and that defines everything from your hiring profile. To your sales playbook, to your demand gen choices, to. A lot of that stuff is contextual. And so hiring is one of those. And when I realized that I can't just copy what John had done at PTC for his top sales hires, and I had to almost engineer, like you said, cap my hiring scorecard, my formula. And so what I did was I sat back and I like the first thing I did. And I do this with all our companies. It's a very useful. They really appreciate the exercise is okay, like, let's look at these. Even if we have, let's just say five salespeople. Okay, so Susan's your number one salesperson. Why is she number one? What makes her great? And then Bob got fired. Why did Bob get fired? Right. What did he struggle with? And as we go through this exercise, what comes out of that are the attributes that are correlated with success, just in a qualitative nature. Okay. And so now that can be translated into a basic scorecard where we list these five to 10 attributes. Coachability, intelligence, curiosity. I know John likes curiosity. You know, like work ethic. Right. And then we don't just want to limit to those two words. Like, let's define, like if we're talking about work ethic, what do we mean by that when we talk about curiosity? Can you define that for me? So let's define that and let's take the time to define what when we meet candidates, what is a high score going to look like for curiosity, what is a medium score going to look like and what is a low score? So we have this rubric, right? And now, like, you know, what does that take me, like, three hours to build? You know what I mean? And now I'm using that and I'm filling that out for all my future hires.
Podcast Narrator
Everyone seems to know our next guest, Chris Stegnin, the original CRO and still the CRO ten years later at Snowflake. In this snippet, Chris echoes the same experiences as Mark Robash did as the first salesperson into a RAW startup. I asked Chris to take us back to those first couple years at Snowflake. And what was his real job responsibilities?
John McMahon
Well, I think, you know, the first thing I did, like the first couple days, I was like, you know, this is the biggest mistake of my life. As I'm sitting there staring across from, like, I actually, you know, sat across from the QA team. So QA engineers, and they're, they're super nice people. But yeah, I was, that was, that was what I was, was going on who I was looking at. And every time I pick up the phone, they're like, will you shut up? Because they were, like, doing their work, right? So I'd have to step outside and walk around and I, And I think I was, I was struggling on exactly what I was supposed to do. And, and you know, Mike Spicer, really, all he cared about was making sure that we got customer feedback. So what I started to do was say, all right, you know, at Avexa, at emc, I would hold my sales team accountable to go on, you know, eight sales calls a week, three, two to three net new business meetings. And so that's what I said I'll do. And so I, I decided, all right, I'm just gonna go out. And even though I, you know, I couldn't put the name of the company on my LinkedIn, you know, we. I had nothing I could send people. I just started, you know, creating spam lists and marketing to a bunch of, you know, Chief Data Officers, CTOs, and saying, look, you know, we've. We've built a database from scratch. And I have, I had a whole spiel, and then I'd ask for 15 minutes and I would go on eight calls a week. And it was all new business meetings for a long time. And John, you were on some of the emails, because every week, not only did I do the eight meetings a week, but I would actually have to send to the entire company, including the board, the summary of my week's activity. And so I really was nervous that I wouldn't. I was so afraid of failure that I would make sure I would do that and I would send a weekly update to the entire team. And to this day, even though we have a retention policy of getting rid of emails that are older than a year, some of the founding engineers, they archive those emails and they kind of hold them as treasure troves because it's a neat thing to go back in time and look back at some of the first meetings I've had with some of our earliest customers. And it's all there in the emails.
Podcast Narrator
Yeah. And if you really. So if we really said in that stage, what is your real job, your job responsibilities, you know, making those eight calls, getting exposure to potential customers. But you, in a, In a funny way, you're a product manager, I'm a.
John McMahon
The early engineers, they jokingly would call me the Shadow cto.
Podcast Narrator
And Chris was in a raw startup with multibillion dollar revenue competitors. Yeah. And what a lot of people don't know is when you started all of this you had some very formidable competitors. Amazon had a product called Redshift. They were probably the leading product in the cloud. And then you had, you know, multi billion dollar companies like Teradata which were on premise companies. But we're trying to make the move to the cloud. So here you are trying to gain product market fit, being basically an evangelist out there. And everywhere you go people are trying to compare you to Teradata and what they probably do in the cloud and to Amazon, a multi billion dollar company with the leading product in the cloud. Can you talk to us a little bit about fighting some of those, you know, major competitors that way?
John McMahon
Yeah, I mean it's, it's daunting, you know, and I think, you know, there's kind of two sides of this is number one is, you know, when you're selling a startup product, people aren't going to give you a ton of money to start. And I think, you know, there's a, there's a misperception if you're a salesperson that you can go into an early stage startup and make a ton of money. And I will tell you that my wife was pretty pissed at me for two years because I had no commissions coming in, right? And I took a pretty big pay cut for probably two and a half years, three years before I could actually make any money because we really weren't selling enough to, to, you know, warrant me taking a commission check. And I think so. So first of all, you know, that was a, that was a kind of a hard grind, if you will, to, to, to start off, you know, doing that and then competing against, you know, the likes of Amazon and Teradata. And you know, there was a series of things that happened that, you know, I always say I'm, you know, better lucky than good. There's a lot of luck that, that I, that I kind of ran into in my career at Snowflake. And the first set of things that that was, was helpful is that Amazon, while they were the first cloud data warehouse with Amazon Redshift, it was not a good product. And so we actually solved a lot of the problems. So what I would do is I would actually build lists and focus on the people that were using Amazon. That was, first of all, I wasn't at the time we would go after the large Teradata customers, but Teradata was the Ferrari of the data warehousing industry. And it was going to be hard for me to really go and take off, you know, take a huge Teradata at the time because we were so small, so I focused on Amazon customers and Amazon Redshift customers. And we would spam them and I would, I identified the pains they had. So I would go in and say, not just me, the entire sales team, we'd go in and say, okay, these are the five or ten things that you have pain around Redshift. And they'd say, yeah, and like we, and I'd say, we solve all these. And, and, and I'm like, don't. Don't believe a thing I say, you know, try it and we'll let you try it for free. So it was like just getting people to try and put data inside a snowflake was, was incredibly hard. And what we would get there and they would try it and they're like, oh, wow, this does solve these problems. So really the first luck, if you will, that I ran into was that Amazon Redshift was not a good product. And then secondarily, as we started to move into the more enterprise y sale, it was really, IBM had this wonderful product called IBM Netezza, that was a separate company. And IBM made the wonderful decision to End of life Neteza, which pissed off all of their customers. So we started targeting Netezza customers. And it was really. The Teradata was the last thing. And I think Teradata, and it's a good lesson for large companies is Teradata was almost arrogant. They're like, you know, Vertica has come along, Ateza's come along. They've never, no one's been ever able to replace Teradata. And, and they were kind of like, we're good. And they ignored the cloud. And they were really like, hey, the cloud's here, but it's way more expensive to store data in the cloud. And they ignored it. So they, they kind of let the cloud sideswipe them. And then we were able, we were there for, for our customers to help them move to the cloud. And, you know, that's really, that was, that's awesome. Because Teradata, you know, sat in their laurels and they didn't respect the competition and they got, they got crushed. And they're, they're getting crushed still here.
Podcast Narrator
Chris gives us an insight into the three things that drive him every day to succeed. One, the overwhelming fear of failure. Two, the mentality that you constantly need to earn your job in order to keep your job. And three, always being open to feedback and learning to adapt.
John McMahon
You know, I, you know, and just to share a personal bit of myself is that, you know, I, I You know, grew up initially, you know, fairly well off going to, sitting at the front row of the, the Celtics games and to, to having nothing like having my house almost taken by the irs, my parents going through this awful divorce and you know, a lot of other stuff. And, and you know, people in general will say, you know, that they can blame other things in their life for their failures. And you know, when I was young, because this was when I was probably 13, 14 years old, I said I want, I'm like, dude, I'm not going to let this define me. I'm not going to let that. So I think from my upbringing I started riding my bike to Star Market in Sudbury, Massachusetts to bag groceries and then to go and get a better paying job. I became a cashier and then I said, oh, I can be a bank teller at baybank, you know, like in, in Sudbury. So, so like I just think, you know, I had him. I, I've had this mentality and I have the mentality to this day is you have to earn your keep every single day and nothing is hand handed to you. And I think the, the biggest issue, you know, cannily of, of people that, that have come from big companies is that they have administrat like I have now. I have everyone kind of doing everything for me and I think what I have, the biggest thing that kind of, the thing that I worry about the most is fear of failure. And so when I came to Snowflake, I wasn't the VP of sales, I was the director of sales. And Mike Spizer told me I'd never be the VP of sales, let alone the CRO. And you know, I, I've just, I've taken the mentality that I have a. I have to earn my job every day, every, you know, month, quarter. And I still keep that same philosophy. There's different things that you have to do as you become a big, you know, as the company grew. And I think the other thing is, you know, I think being super open to feedback is like, you know, I don't know any everything. And I'm gonna like, people are gonna punch me in the mouth and tell me I'm screwing something up and I'm gonna be like, okay, I'm gonna go fix that. And I think John would tell you like, he'd be like, hey buddy, you're gonna, you're gonna. If this, if you don't fix this, it's gonna get fixed another way. And I think John certainly was part of the board discussions where, you know, Spizer Was, was certainly pushing to replace me and bring in a, you know, a more senior person, you know, a more senior person, you know.
Podcast Narrator
And here Cap asks Chris to give advice to startups that are currently landing deals with small companies, but they also want to make the shift to landing deals with very large enterprise companies.
John McMahon
Yeah, so there's kind of two sides of that because you know, I had, I had a leader on the east and a leader on the west that were running almost double very different businesses. And I'm a velocity guy, so I like velocity, I like transactions. Like that is at the heart of it. I want new customer logos. The guy on the east, he got starry eyed with large enterprise and he only wanted to sell the large enterprise. And I think you can't do one or the other, you have to do both. And I think that's, that's the lesson I learned is like, dude, the large enterprise is wonderful, but they'll, they'll, they'll surprise you in the upside one quarter and they'll surprise you on the downside in a material way the next quarter. So if you build a business just on the large enterprise, you're screwed. And to this day my largest market is in the west because we opened up the most amount of logos in the west so that just getting new logos matters. And anyone who tells me they're just going to sell the large enterprise, as a salesperson, I would have zero interest in selling to just the large enterprise.
Podcast Narrator
In this clip, Cedric pesh CRO@mongodb shares. The reason why giving your sales team a purpose is so very important to not only the short term but the long term motivation of the team. And you touched on this a little bit. But you've done an amazing job getting your team to bond as one and then buy into the team's purpose, which I think is really important because a lot of people are always sitting back asking why am I doing what I'm doing? Especially during COVID a lot of people ask that.
John Kaplan
Yes.
Podcast Narrator
Yeah. Can you talk a little bit about why purpose is so important to the team and the motivation of the team?
John Kaplan
I think it starts from you, meaning there is a moment where you wake up in the morning and it's so hard that you ask yourself why am I doing what I'm doing? And the moment you start asking that, then you start needing to dig into yourself and do some introspection to come up with answers. And sometimes you don't come up with answers and therefore it's too hard and not worth it. And sometimes you do come up with answers, then from the moment you come up with answers for yourself, then it's about how do I articulate that to the rest of my team? And are others feeling the same thing? Because you do push. The more indexed you are on execution, the more you push your people to the brink, the more they do ask that question to themselves as well. If they are intelligent, right?
Podcast Narrator
Sure.
John Kaplan
And they are obviously very intelligent. So then it's really about doing the work together with the team to come up with collective answers, personal answers to these questions. Why, as a VP of North America, am I doing what I'm doing and working 60 hours a week and going through the pain that it takes to do that? What is motivating me? And as a team, what values do we stand for? If we say we stand for excellence and innovation, what does that mean practically for the people working around us, what's in it for them? How are they going to benefit from us building an excellent, outstanding team or us being committed to innovation in their day to day work? So all this work of, let's say, team introspection as well as personal introspections as senior leaders, I think it's very important because, you know, now I start seeing the world of sales leaders in three buckets, right? You've got the, you've got the sales leaders who promise a great paycheck and a couple of trainings. And in 2021, frankly, these leaders fall in the category of those which don't really know what they are doing. So let's draw them and focus on the others, right? But the remaining ones, you have these two categories. You have these leaders which are super sharp on, you know, defining the messaging and the ideal customer profile, the market. You want to focus on the recruiting profiles and productivity models and all these things which are very important tools, but they are all execution oriented, right? And then you have this. And if you have this is very, very, very important to excel at that from the execution standpoint. But if you don't go beyond that and don't explain your people, why is it that they need to excel on that side of things, sales, execution rather than qualification, and so on and so forth, then they really quickly start feeling that this is a grinding organization, all focused on execution and not very inspiring. And the next thing you know is that they are here exclusively for a paycheck which needs to be there anyways, but it's never enough. There is a moment where if it's only about the paycheck, the team starts saying, I can't take that. It's too hard, at least if you pretend to excel. And this is where I think the third category of leaders come, or at least sales organizations come, which really work on defining that vision. And it's quite a journey. You don't show up a morning and you say, I'm going to write my vision on the wall or my team vision on the wall. And then I'm going. It's a little like. And if you don't do that, it's a huge waste of energy in the, like, it's a little like, you know, Martin Luther King saying I have a dream. And then turning to the crowd and saying, and my dream is that you guys are all going to make a lot of money. It's a little like that, right? It's odd. It's weird, right? So there is this whole process of working together in order to come up. I have a dream. Let's define that dream. Let's see if this is authentic, it's us or it's someone else dream. And how are we going to execute on it and how is this connected to tomorrow morning and what we are going to do tomorrow morning? That's a lot of work.
John McMahon
And your point is on the dream.
John Kaplan
Part, when you're the leader.
John McMahon
It'S got to be a big enough dream that people are going to be willing to sacrifice.
John Kaplan
People are going to be willing to.
John McMahon
Put in the grind.
Mark Roberge
People are going to be willing to.
John Kaplan
Do things that they just normally wouldn't do.
Mark Roberge
So the dream has to be big enough and meaningful enough.
John Kaplan
There is this quote from this French author, John, which used to say that if you want to build a ship, don't drum up people to collect wood and don't assign them task and work only, but rather teach them to long for the endless immensity of the sea.
Mark Roberge
Yeah.
John Kaplan
So, you know, it's. When you define the sales process, when you train people on it and qualifying things, these are all incredibly important things to do without which there is no way to build anything. Right. Like, it's about gathering the wood and, and giving the task and so on, so forth, right. You make them competent at doing that, but the more you grind them on that, the more you push excellence in execution, the more you need to remind them every day about the. What the immensity of the sea looks like. Otherwise, those guys are. After a while, they are like, you know, I'm screw driving. I've been screw driving for four days here, five days. I forgot why I was, what I was building, right? I Don't even understand. I was building a ship and I was supposed to sail on the endless ocean one day. So as a leadership team, you do need to be able to define what that endless ocean looks like and how are we going to get there all together and what does a ship look like? And keep that vision always connected.
Podcast Narrator
Here Cedric shares a fantastic story of how his first line sales manager, Carlo, handled Cedric when Cedric was going to quit the company. Now I need to give you a little more background. Cedric is French, he's in his early 20s and he's living in Bologna, Italy where he's learning how to speak Italian and English. And Cedric had chosen to work for Carlo in Italy because he had heard that Carlo was the best first line sales manager in all of Europe. But Cedric was living in a small apartment in a strange city where he doesn't speak the language and he's trying to make sales calls using a foreign language. It all becomes very overwhelming. So Cedric's going to quit and here's Cedric telling the story.
John Kaplan
It's over, right? So I'm sitting in my desk 7:30 in the morning and he's supposed to show up at 7:30 and you know, I'm sweating like, holy shit. He gets into the office and instead of turning right back into his own office, he's very smart. He sees me there and probably my body language was betraying me. He goes straight to my office, but he stares in mine and goes like, how are you doing? And I'm starting to mumble. And Carlo, I think I might have not made the right decision for myself. And before I end up, I finish my sentence, he goes like, where are you living those days? And I'm like, you should know that because you signed my expense reports. I'm in a hotel in the suburbs of Bologna and that's where I am. And he stops me and goes like, you're going to stop here. Gonna take three days off, gonna go and find an apartment for yourself. And once you are settled and in a good place, you come back to work. I don't want to see you before that.
Podcast Narrator
His intuition was off the charts.
John Kaplan
Yeah, yeah, yeah, 100%. But like, as far as I was concerned, it wasn't really the direction I wanted to take that conversation to. Wild, right? So I'm like, I'm like, holy shit. So I try last one and I tell him, which was the truth. I don't have the money to make a down payment to get that apartment anyway, so it's not an option. I was trying to Work myself out of this conversation. And before I can understand what's going on, he pulls out his paycheck and writes a 3 million lir check, which was probably at the time the largest check I had ever seen. And he hands me over his check and I'm like, I've known you for two months. I don't do that. And by the way, I'll never be able to give you this money back, Carlo. And the guy has that line which does differentiate great leaders from others. At the right moment, in the right place, he goes, you are going to give me that money back when you get your first commissions. And I'm sitting on my chair in a long moment of loneliness because this guy believes in me more than more than I believe in myself.
Podcast Narrator
That's powerful.
John Kaplan
And therefore I'm like, I can't give up on this guy. I can't quit on this guy. I just can't watch myself in the mirror in the morning. And that has been an important lesson for me as I reflected about it when I grew up in my career. Because at the end of the day, we are not in the software business. We are in the people business, right? And to the extent that us as leaders can actually get involved authentically, not talking about faking it, but authentically in being curious about what's going on in our team's life. And actually it's a buzzword like caring about them and making a difference that does that can have a giant motivational impact on people. It had on me for sure, and I never forgot it, right? We worked 10 years together and never, never, ever. I'm very, very bad at taking directions. I'm pretty good at taking inputs. I was very difficult to handle and he was able to build a partnership with me which I will have never betrayed at any price. And that's what happened here.
Podcast Narrator
Cedric shares two powerful insights for young salespeople. First, work on your sales craft with an understanding that your success will be determined over the long term, not the short term. And second, how to deal with three different types of sales leaders. A great sales leader, an average sales leader, and a bad sales leader.
John Kaplan
I will give them. The first piece of advice I will give them is exactly what the entire enterprise software sales corporate world is not doing, which is be patient and work on your craft and don't cut corners and don't go after the next promotion or after short term money, but really work on your foundations. Because this is a marathon, right? If your ambition is to being amazing at what you do in the long Term, you're not going to win or lose in the next couple of quarters. You're going to win in the next 20 years, 15 years, 10 years, that's what you're going to do. And unfortunately, the whole world is trying to make people believe that they should be rushing into promotions and bigger titles and more money in the short term. And I think it's a giant mistake because it's like. Is betraying those.
Mark Roberge
Those.
John Kaplan
Those young, young people, right? That's one piece of advice which is very difficult to give because most of the time, people I'm not sure I will have. I was able to listen to this one, even if it was given to me many times, including by Carlo. I had a hard time listening to it. And I wish I could talk to the. To those people with. To these younger salespeople with the eyes and the experience I have right now, because, you know, it's too bad. I saw so many mistakes there. The other piece of advice I will tell them is that out of all the leaders I've worked with, let's call it this way, I've got 20 to 30% of them which were really bad. Maybe, you know, 40% which were. Whether they were there or not will not change anything. And then I've got maybe 10, 15% which were amazing. Now, the way to deal with the amazing leaders is easy, right? You get inspired, you observe, you listen, and you try to work on yourself and you imitate someone, and that's an easy one. The vast majority of those leaders are there which are without any color. They don't hurt, but they don't add any value. You need to be able to use them. By using them, I mean, I give you something to execute on you do it for me so that they can do my job. And as a young salesperson, you need to recognize that, right? It's not because your leader doesn't add values that you can't still progress your career. And the third piece I would say is when you bump into a bad leader, that's another learning opportunity about when you're going to be in his or her shoes. Here's what you'll never do. Here's what you are going to avoid at any cost, right? And you suffer the pain out of it, and it's horrible. And this is why it's an even better lesson. And that happened to me many times.
Podcast Narrator
Cedric is originally from Les Deux Alps in France, and before Cedric's sales career, he was on the French national downhill ski team here. I asked Cedric about paying attention to details. And I love his answer where he shares that water boils at 100 degrees centigrade, not 98 degrees, and how there's a huge difference in those two degrees. This is so very true. In many instances when sales teams try to implement the new sales process or qualification methodology, Cedric believes the details will determine the result if it fails. Most times it was in the execution of the details of the process, not the process itself. Hey, Cedric, I've also known you to be very detail oriented and I always wondered, did that go. And it must go back to. Before you're going to go strap on some skis and go downhill at 90 miles an hour, you better pay attention to the details.
John Kaplan
Yes, yes, yes. 100%. I think that. I think there are two sides there. There is one which is. There are big consequences which are hiding in the details if you don't take care of them. That's your point, I guess. Right. Like potentially, you know, between 98 degrees where water doesn't boil and 100 degrees, there is a difference. And those two degrees are actually incredibly important. And it's true when you. I see many times teams implementing a process and then getting to a conclusion and say the process doesn't work. But then you never know if this is execution of the process which doesn't work or the process itself. Right. And I think the other aspect of this is I do believe that greatness in sales implies or requires a lot of curiosity, like intellectual curiosity and curiosity has to do with details.
Podcast Narrator
Well, we had some great insights here from some of the best in the industry. We were really happy to feature them on Revenue Builders. Thanks again to all our listeners for listening to another episode of the Revenue Builders. Thanks for listening to today's episode.
John Kaplan
Be sure to check us out@ForceManagement.com.
Episode: Best Practices from Elite Sales Leaders
Date: July 6, 2023
Hosts: John McMahon & John Kaplan
Guests: Mark Roberge (HubSpot, Stage 2 Capital), Chris Degnan (Snowflake), Cedric Pesh (MongoDB)
This episode curates practical, hard-won wisdom from top Chief Revenue Officers about what it really takes to build and scale high-performing sales teams. The hosts dive deep into the realities of being the first sales hire at a startup, the critical importance of hiring, the role of purpose in sales teams, retaining top performers, and why meticulous execution matters. Through vivid stories and candid advice, listeners get actionable takeaways and a behind-the-scenes look at the journeys of elite CROs.
Mark Roberge (HubSpot)
Notable Quote:
“I personally don’t think pricing matters a lot right there. I think you’re just trying to get people in and create success stories and you’re trying to get good market learnings back to the product team.”
— Mark Roberge (03:45)
Mark Roberge (HubSpot)
Notable Quote:
“The job of salesperson and manager is so different… So I put together a process: step number one, hit your quota six months in a row... then you go into leadership school, then you coach a new hire for three months alongside your quota.”
— Mark Roberge (07:32)
Mark Roberge (HubSpot)
Notable Quote:
“There is no universal top sales hire profile. It’s very contextual to your go-to-market context… So hiring is one of those.”
— Mark Roberge (10:43)
Chris Degnan (Snowflake)
Notable Quote:
“There’s a misperception… you can go into an early-stage startup and make a ton of money. I will tell you, my wife was pretty pissed at me for two years because I had no commissions coming in.”
— Chris Degnan (18:10)
Chris Degnan (Snowflake)
Describes his core motivations:
Chris Degnan (Snowflake)
Notable Quote:
“The large enterprise is wonderful, but they’ll surprise you in the upside one quarter and they’ll surprise you on the downside the next quarter. If you build a business just on the large enterprise, you’re screwed.”
— Chris Degnan (25:29)
Cedric Pesh (MongoDB)
Notable Quote:
“If it’s only about the paycheck, the team starts saying, I can’t take that. It’s too hard, at least if you pretend to excel... There is this whole process of working together to come up... I have a dream. Let’s define that dream. Let’s see if this is authentic, it’s us or it’s someone else’s dream.”
— Cedric Pesh (30:22)
Cedric Pesh (MongoDB)
Notable Quote:
“This guy believes in me more than I believe in myself… I can’t give up on this guy. I can’t quit on this guy.”
— Cedric Pesh (36:01)
Cedric Pesh (MongoDB)
Notable Quote:
“Your ambition is to be amazing at what you do in the long term. You’re not going to win or lose in the next couple quarters, you’re going to win in the next 20 years.”
— Cedric Pesh (38:40)
Cedric Pesh (MongoDB)
Notable Quote:
“Between 98 degrees where water doesn’t boil and 100 degrees, there is a difference. And those two degrees are actually incredibly important… Greatness in sales requires a lot of curiosity and curiosity has to do with details.”
— Cedric Pesh (42:20)
This episode delivers raw insights from leaders who've built sales machines from zero at breakout tech companies. Listeners are encouraged to focus on hiring for potential, develop leaders internally, inspire teams with meaningful vision, pay close attention to execution, and measure their careers not by their last quarter, but over decades. Human care and curiosity, not just process and numbers, are the secret ingredients to enduring sales success.